CA1109077A - 2-hydrazonopropionic acid derivatives and the preparation thereof - Google Patents
2-hydrazonopropionic acid derivatives and the preparation thereofInfo
- Publication number
- CA1109077A CA1109077A CA309,492A CA309492A CA1109077A CA 1109077 A CA1109077 A CA 1109077A CA 309492 A CA309492 A CA 309492A CA 1109077 A CA1109077 A CA 1109077A
- Authority
- CA
- Canada
- Prior art keywords
- propionic acid
- chain
- acid
- saturated
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- KHIQJCVGWNEQMI-DJWKRKHSSA-N (2z)-2-hydrazinylidenepropanoic acid Chemical class N/N=C(/C)C(O)=O KHIQJCVGWNEQMI-DJWKRKHSSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 150000005599 propionic acid derivatives Chemical class 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- -1 2-(octylhydrazono)-propionic acid Chemical compound 0.000 claims description 46
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 28
- 229940107700 pyruvic acid Drugs 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- IPGKROMWTLUUOT-UKTHLTGXSA-N (2e)-2-(2-cyclohexylethylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(/C)=N/NCCC1CCCCC1 IPGKROMWTLUUOT-UKTHLTGXSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- NTSMBVBKRTVSFJ-UHFFFAOYSA-N 2-(3-cyclopentylpropylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCCC1CCCC1 NTSMBVBKRTVSFJ-UHFFFAOYSA-N 0.000 claims description 3
- QVRJSUUYYFZCFZ-UHFFFAOYSA-N 2-(4-methylhexylhydrazinylidene)propanoic acid Chemical compound CCC(C)CCCNN=C(C)C(O)=O QVRJSUUYYFZCFZ-UHFFFAOYSA-N 0.000 claims description 3
- KHTXCMBZBJTRBZ-UHFFFAOYSA-N 2-(hex-4-enylhydrazinylidene)propanoic acid Chemical compound CC=CCCCNN=C(C)C(O)=O KHTXCMBZBJTRBZ-UHFFFAOYSA-N 0.000 claims description 3
- XLVSIZGEIKTDKG-UHFFFAOYSA-N 2-cyclohexylethylhydrazine;sulfuric acid Chemical compound OS(O)(=O)=O.NNCCC1CCCCC1 XLVSIZGEIKTDKG-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- FOGSUMCAZCGOQX-UHFFFAOYSA-N 3-cyclopentylpropylhydrazine;hydrochloride Chemical compound Cl.NNCCCC1CCCC1 FOGSUMCAZCGOQX-UHFFFAOYSA-N 0.000 claims description 2
- CAGACUWDXQTGKT-UHFFFAOYSA-N 4-methylhexylhydrazine;dihydrochloride Chemical compound Cl.Cl.CCC(C)CCCNN CAGACUWDXQTGKT-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- CJXNGKPHBHRQEU-UHFFFAOYSA-N hex-4-enylhydrazine;hydrochloride Chemical compound Cl.CC=CCCCNN CJXNGKPHBHRQEU-UHFFFAOYSA-N 0.000 claims description 2
- RRIJZRZUKBIERI-UHFFFAOYSA-N hexylhydrazine;hydrochloride Chemical compound Cl.CCCCCCNN RRIJZRZUKBIERI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- QAIUKOKJKLIFAP-UHFFFAOYSA-N octylhydrazine;hydrochloride Chemical compound Cl.CCCCCCCCNN QAIUKOKJKLIFAP-UHFFFAOYSA-N 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 abstract description 11
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 6
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 6
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229940095574 propionic acid Drugs 0.000 description 5
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229960000964 phenelzine Drugs 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SZKZAWOWHNTOOQ-UHFFFAOYSA-N 3-cyclohexylpropylhydrazine;hydrochloride Chemical compound Cl.NNCCCC1CCCCC1 SZKZAWOWHNTOOQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- HHRZAEJMHSGZNP-UHFFFAOYSA-N mebanazine Chemical compound NNC(C)C1=CC=CC=C1 HHRZAEJMHSGZNP-UHFFFAOYSA-N 0.000 description 2
- 229950006217 mebanazine Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- LEPFDJZATUOEPP-UHFFFAOYSA-N nonylhydrazine;hydrochloride Chemical compound Cl.CCCCCCCCCNN LEPFDJZATUOEPP-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FFVMXOZLLAHGEJ-UHFFFAOYSA-M sodium;2-(pentylhydrazinylidene)propanoate Chemical compound [Na+].CCCCCNN=C(C)C([O-])=O FFVMXOZLLAHGEJ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- ZCRXJCODBRQIKD-UHFFFAOYSA-N 1-(3-cyclohexylprop-1-enyl)-1-methylhydrazine;hydrochloride Chemical compound Cl.CN(N)C=CCC1CCCCC1 ZCRXJCODBRQIKD-UHFFFAOYSA-N 0.000 description 1
- PMDFEGLHKZBZBB-UHFFFAOYSA-N 2-(2-cycloheptylethylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCC1CCCCCC1 PMDFEGLHKZBZBB-UHFFFAOYSA-N 0.000 description 1
- SAVMSLHOOJTVJR-UHFFFAOYSA-N 2-(2-cyclohex-3-en-1-ylethylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCC1CCC=CC1 SAVMSLHOOJTVJR-UHFFFAOYSA-N 0.000 description 1
- BOHVIWUFHXRQHD-UHFFFAOYSA-N 2-(2-cyclopentylethylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCC1CCCC1 BOHVIWUFHXRQHD-UHFFFAOYSA-N 0.000 description 1
- APULSDJLVFGJHG-UHFFFAOYSA-N 2-(2-ethylbutylhydrazinylidene)propanoic acid Chemical compound CCC(CC)CNN=C(C)C(O)=O APULSDJLVFGJHG-UHFFFAOYSA-N 0.000 description 1
- LUNXTKMYBXHPSU-UHFFFAOYSA-N 2-(2-ethylhexylhydrazinylidene)propanoic acid Chemical compound CCCCC(CC)CNN=C(C)C(O)=O LUNXTKMYBXHPSU-UHFFFAOYSA-N 0.000 description 1
- XCKUNPKWWVMURZ-UHFFFAOYSA-N 2-(2-methylpropylhydrazinylidene)propanoic acid Chemical compound CC(C)CNN=C(C)C(O)=O XCKUNPKWWVMURZ-UHFFFAOYSA-N 0.000 description 1
- LZTTXWHJWGFZRC-UHFFFAOYSA-N 2-(3,3-dimethylbutylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCC(C)(C)C LZTTXWHJWGFZRC-UHFFFAOYSA-N 0.000 description 1
- HUYGLVGPKQTLET-UHFFFAOYSA-N 2-(3-cyclohexylpropylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCCC1CCCCC1 HUYGLVGPKQTLET-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- YEAMDJSQTCOJTI-UHFFFAOYSA-N 2-(3-methylbutylhydrazinylidene)propanoic acid Chemical compound CC(C)CCNN=C(C)C(O)=O YEAMDJSQTCOJTI-UHFFFAOYSA-N 0.000 description 1
- YFSHRWXCGAQHPZ-UHFFFAOYSA-N 2-(4-methylpentylhydrazinylidene)propanoic acid Chemical compound CC(C)CCCNN=C(C)C(O)=O YFSHRWXCGAQHPZ-UHFFFAOYSA-N 0.000 description 1
- NDEFYBJKCSDMFJ-UHFFFAOYSA-N 2-(5-methylhexylhydrazinylidene)propanoic acid Chemical compound CC(C)CCCCNN=C(C)C(O)=O NDEFYBJKCSDMFJ-UHFFFAOYSA-N 0.000 description 1
- JWXDVIWEKUBVIB-UHFFFAOYSA-N 2-(but-3-enylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCC=C JWXDVIWEKUBVIB-UHFFFAOYSA-N 0.000 description 1
- QLSFQXOVODLAHV-UHFFFAOYSA-N 2-(cyclohexylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNC1CCCCC1 QLSFQXOVODLAHV-UHFFFAOYSA-N 0.000 description 1
- BWPBYHRJHWYWRY-UHFFFAOYSA-N 2-(dec-9-enylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCCCCCCCC=C BWPBYHRJHWYWRY-UHFFFAOYSA-N 0.000 description 1
- BDWGVKUAMYSKQW-UHFFFAOYSA-N 2-(decylhydrazinylidene)propanamide Chemical compound CCCCCCCCCCNN=C(C)C(N)=O BDWGVKUAMYSKQW-UHFFFAOYSA-N 0.000 description 1
- VPWLXKNCZAMGDH-UHFFFAOYSA-N 2-(decylhydrazinylidene)propanoic acid Chemical compound CCCCCCCCCCNN=C(C)C(O)=O VPWLXKNCZAMGDH-UHFFFAOYSA-N 0.000 description 1
- QZHWESTUQGGHJL-UHFFFAOYSA-N 2-(dodecylhydrazinylidene)propanoic acid Chemical compound CCCCCCCCCCCCNN=C(C)C(O)=O QZHWESTUQGGHJL-UHFFFAOYSA-N 0.000 description 1
- MRNGTPYCVLTQEK-UHFFFAOYSA-N 2-(heptan-2-ylhydrazinylidene)propanoic acid Chemical compound CCCCCC(C)NN=C(C)C(O)=O MRNGTPYCVLTQEK-UHFFFAOYSA-N 0.000 description 1
- RLBVXEJQICRODO-UHFFFAOYSA-N 2-(hex-1-enylhydrazinylidene)propanoic acid Chemical compound CCCCC=CNN=C(C)C(O)=O RLBVXEJQICRODO-UHFFFAOYSA-N 0.000 description 1
- FRHFHOUXONAWCG-UHFFFAOYSA-N 2-(hex-3-enylhydrazinylidene)propanoic acid Chemical compound CCC=CCCNN=C(C)C(O)=O FRHFHOUXONAWCG-UHFFFAOYSA-N 0.000 description 1
- IDHDJZAAXWYJSA-UHFFFAOYSA-N 2-(hex-5-enylhydrazinylidene)propanoic acid Chemical compound OC(=O)C(C)=NNCCCCC=C IDHDJZAAXWYJSA-UHFFFAOYSA-N 0.000 description 1
- KUSQXACIGUDUMF-UHFFFAOYSA-N 2-(octadecylhydrazinylidene)propanoic acid Chemical compound CCCCCCCCCCCCCCCCCCNN=C(C)C(O)=O KUSQXACIGUDUMF-UHFFFAOYSA-N 0.000 description 1
- NOWVKRUUEXTWPW-UHFFFAOYSA-N 2-(pent-3-enylhydrazinylidene)propanoic acid Chemical compound CC=CCCNN=C(C)C(O)=O NOWVKRUUEXTWPW-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- NETWAMWHZFFNDL-UHFFFAOYSA-N 2-cycloheptylethylhydrazine;hydrochloride Chemical compound Cl.NNCCC1CCCCCC1 NETWAMWHZFFNDL-UHFFFAOYSA-N 0.000 description 1
- YKONFNRNHKTUDJ-UHFFFAOYSA-N 2-cyclohex-3-en-1-ylethylhydrazine;hydrochloride Chemical compound Cl.NNCCC1CCC=CC1 YKONFNRNHKTUDJ-UHFFFAOYSA-N 0.000 description 1
- HKIVTJOODWTEBW-UHFFFAOYSA-N 2-cyclohexylethylhydrazine Chemical compound NNCCC1CCCCC1 HKIVTJOODWTEBW-UHFFFAOYSA-N 0.000 description 1
- ABPQIOPWPZVSQT-UHFFFAOYSA-N 2-cyclopentylethylhydrazine;hydrochloride Chemical compound Cl.NNCCC1CCCC1 ABPQIOPWPZVSQT-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- QAKPXFWHGDVTLG-UHFFFAOYSA-N 2-ethylbutylhydrazine;hydrochloride Chemical compound Cl.CCC(CC)CNN QAKPXFWHGDVTLG-UHFFFAOYSA-N 0.000 description 1
- SUFNSZIJMAMLCJ-UHFFFAOYSA-N 2-ethylhexylhydrazine Chemical compound CCCCC(CC)CNN SUFNSZIJMAMLCJ-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- HIOPKCFEHPXYPY-UHFFFAOYSA-N 2-methylpropylhydrazine;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)CNN HIOPKCFEHPXYPY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GHRBRHSMUPEADI-UHFFFAOYSA-N 3,3-dimethylbutylhydrazine;hydrochloride Chemical compound Cl.CC(C)(C)CCNN GHRBRHSMUPEADI-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- WHWIJTYMEOCDFT-UHFFFAOYSA-N 3-cyclohexylprop-1-enylhydrazine;hydrochloride Chemical compound Cl.NNC=CCC1CCCCC1 WHWIJTYMEOCDFT-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- ZGISDJPJIHAFON-UHFFFAOYSA-N 3-methylbutylhydrazine;hydrochloride Chemical compound Cl.CC(C)CCNN ZGISDJPJIHAFON-UHFFFAOYSA-N 0.000 description 1
- XRNVYUHUWFFLJS-UHFFFAOYSA-N 3-methyloctylhydrazine;oxalic acid Chemical compound OC(=O)C(O)=O.CCCCCC(C)CCNN XRNVYUHUWFFLJS-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- ZCTZGENJYZPMAK-UHFFFAOYSA-N 4-methylpentylhydrazine;hydrochloride Chemical compound Cl.CC(C)CCCNN ZCTZGENJYZPMAK-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- IZQGLYQLXCYWGO-UHFFFAOYSA-N 5-methylhexylhydrazine;hydrochloride Chemical compound Cl.CC(C)CCCCNN IZQGLYQLXCYWGO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772739380 DE2739380A1 (de) | 1977-09-01 | 1977-09-01 | N-substituierte 2-hydrazono-propionsaeure-derivate, verfahren zur herstellung derselben und arzneimittel, die diese enthalten |
| DEP2739380.2 | 1977-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109077A true CA1109077A (en) | 1981-09-15 |
Family
ID=6017861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,492A Expired CA1109077A (en) | 1977-09-01 | 1978-08-16 | 2-hydrazonopropionic acid derivatives and the preparation thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4206231A (en, 2012) |
| EP (1) | EP0001144B1 (en, 2012) |
| JP (1) | JPS5452028A (en, 2012) |
| AR (1) | AR216531A1 (en, 2012) |
| AT (1) | AT363454B (en, 2012) |
| AU (1) | AU516223B2 (en, 2012) |
| CA (1) | CA1109077A (en, 2012) |
| CS (1) | CS199744B2 (en, 2012) |
| DD (1) | DD138652A5 (en, 2012) |
| DE (2) | DE2739380A1 (en, 2012) |
| DK (1) | DK147197C (en, 2012) |
| ES (1) | ES472749A1 (en, 2012) |
| FI (1) | FI66843C (en, 2012) |
| HU (1) | HU177956B (en, 2012) |
| IE (1) | IE47260B1 (en, 2012) |
| IL (1) | IL55427A (en, 2012) |
| IT (1) | IT1098384B (en, 2012) |
| PL (1) | PL111073B1 (en, 2012) |
| PT (1) | PT68483A (en, 2012) |
| SU (1) | SU725555A1 (en, 2012) |
| YU (1) | YU204778A (en, 2012) |
| ZA (1) | ZA784969B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031842A1 (de) * | 1980-08-23 | 1982-04-08 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-substituierte brenztraubensaeurehydrazone, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| DE3036281A1 (de) | 1980-09-26 | 1982-05-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | 0-substituierte brenztraubensaeureoxime, verfahren zu ihrer herstellung, ihre verwendung sowie arzneimittel, die diese verbindungen enthalten |
| WO1986000522A1 (en) * | 1984-07-17 | 1986-01-30 | Boehringer Mannheim Gmbh | UTILIZATION OF alpha-CETOCARBONIC ACID HYDRAZONES AND OXINES FOR TREATING CARDIAC OR CIRCULATORY DISEASES |
| CA2535403A1 (en) * | 2003-08-08 | 2005-02-17 | La Jolla Pharmaceutical Company | Inhibitors of semicarbazide-sensitive amine oxidase (ssao) and vap-1 mediated adhesion useful for treatment of diseases |
| WO2006041922A2 (en) * | 2004-10-08 | 2006-04-20 | Dara Biosciences, Inc. | Agents and methods for administration to the central nervous system |
| WO2006088798A2 (en) * | 2005-02-14 | 2006-08-24 | Albert Einstein College Of Medicine Of Yeshiva University | Modulation of hypothalamic atp-sensitive potassium channels |
| US8242058B2 (en) * | 2006-07-21 | 2012-08-14 | Wisconsin Alumni Research Foundation | Reagents and methods for appending functional groups to proteins |
| US9047945B2 (en) | 2012-10-15 | 2015-06-02 | Marvell World Trade Ltd. | Systems and methods for reading resistive random access memory (RRAM) cells |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2643303A1 (de) * | 1976-09-25 | 1978-03-30 | Haeckel Rainer | Hypoglykaemisch wirksames arzneimittel |
| CA1106389A (en) * | 1976-09-25 | 1981-08-04 | Rainer Haeckel | 2-(phenylalkylhydrazono)-propionic acid derivatives and the preparation thereof |
-
1977
- 1977-09-01 DE DE19772739380 patent/DE2739380A1/de not_active Withdrawn
-
1978
- 1978-08-16 CA CA309,492A patent/CA1109077A/en not_active Expired
- 1978-08-17 US US05/934,291 patent/US4206231A/en not_active Expired - Lifetime
- 1978-08-22 ES ES472749A patent/ES472749A1/es not_active Expired
- 1978-08-23 FI FI782574A patent/FI66843C/fi not_active IP Right Cessation
- 1978-08-24 IL IL55427A patent/IL55427A/xx unknown
- 1978-08-24 DK DK373478A patent/DK147197C/da not_active IP Right Cessation
- 1978-08-24 AU AU39233/78A patent/AU516223B2/en not_active Expired
- 1978-08-24 SU SU2652698A patent/SU725555A1/ru active
- 1978-08-25 DD DD78207485A patent/DD138652A5/xx unknown
- 1978-08-25 AR AR273447A patent/AR216531A1/es active
- 1978-08-28 PL PL1978209256A patent/PL111073B1/pl unknown
- 1978-08-28 IT IT27078/78A patent/IT1098384B/it active
- 1978-08-28 PT PT68483A patent/PT68483A/pt unknown
- 1978-08-29 AT AT0627478A patent/AT363454B/de not_active IP Right Cessation
- 1978-08-29 DE DE7878200166T patent/DE2860777D1/de not_active Expired
- 1978-08-29 EP EP78200166A patent/EP0001144B1/de not_active Expired
- 1978-08-29 YU YU02047/78A patent/YU204778A/xx unknown
- 1978-08-30 HU HU78BO1732A patent/HU177956B/hu unknown
- 1978-08-31 CS CS785653A patent/CS199744B2/cs unknown
- 1978-08-31 ZA ZA00784969A patent/ZA784969B/xx unknown
- 1978-08-31 IE IE1756/78A patent/IE47260B1/en unknown
- 1978-09-01 JP JP10743578A patent/JPS5452028A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI782574A7 (fi) | 1979-03-02 |
| AT363454B (de) | 1981-08-10 |
| EP0001144B1 (de) | 1981-06-17 |
| JPS6218545B2 (en, 2012) | 1987-04-23 |
| US4206231A (en) | 1980-06-03 |
| AR216531A1 (es) | 1979-12-28 |
| DK147197C (da) | 1984-10-29 |
| IL55427A (en) | 1981-12-31 |
| JPS5452028A (en) | 1979-04-24 |
| DE2739380A1 (de) | 1979-03-08 |
| FI66843B (fi) | 1984-08-31 |
| AU516223B2 (en) | 1981-05-21 |
| EP0001144A1 (de) | 1979-03-21 |
| DK373478A (da) | 1979-03-02 |
| DK147197B (da) | 1984-05-14 |
| IL55427A0 (en) | 1978-10-31 |
| IE781756L (en) | 1979-03-01 |
| HU177956B (en) | 1982-02-28 |
| AU3923378A (en) | 1980-02-28 |
| YU204778A (en) | 1982-10-31 |
| IT1098384B (it) | 1985-09-07 |
| IT7827078A0 (it) | 1978-08-28 |
| IE47260B1 (en) | 1984-02-08 |
| CS199744B2 (en) | 1980-07-31 |
| ZA784969B (en) | 1979-09-26 |
| ES472749A1 (es) | 1979-02-16 |
| PL209256A1 (pl) | 1979-06-04 |
| DE2860777D1 (en) | 1981-09-24 |
| PL111073B1 (en) | 1980-08-30 |
| DD138652A5 (de) | 1979-11-14 |
| SU725555A3 (en) | 1980-03-30 |
| SU725555A1 (ru) | 1980-03-30 |
| PT68483A (de) | 1978-09-01 |
| ATA627478A (de) | 1981-01-15 |
| FI66843C (fi) | 1984-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |